WO2004041226A1 - Agents contenant des derives de 4-amino-biphenyl-3-ol permettant de colorer des fibres de keratine - Google Patents

Agents contenant des derives de 4-amino-biphenyl-3-ol permettant de colorer des fibres de keratine Download PDF

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Publication number
WO2004041226A1
WO2004041226A1 PCT/EP2003/004960 EP0304960W WO2004041226A1 WO 2004041226 A1 WO2004041226 A1 WO 2004041226A1 EP 0304960 W EP0304960 W EP 0304960W WO 2004041226 A1 WO2004041226 A1 WO 2004041226A1
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WO
WIPO (PCT)
Prior art keywords
amino
biphenyl
chloro
methyl
group
Prior art date
Application number
PCT/EP2003/004960
Other languages
German (de)
English (en)
Inventor
Laurent Chassot
Hans-Jürgen BRAUN
Original Assignee
Wella Aktiengesellschaft
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Wella Aktiengesellschaft filed Critical Wella Aktiengesellschaft
Priority to JP2004548708A priority Critical patent/JP2006511496A/ja
Priority to AU2003227748A priority patent/AU2003227748A1/en
Priority to US10/501,833 priority patent/US7122061B2/en
Priority to BR0306686-0A priority patent/BR0306686A/pt
Priority to EP03725188A priority patent/EP1562539A1/fr
Publication of WO2004041226A1 publication Critical patent/WO2004041226A1/fr

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Classifications

    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/69—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing fluorine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/41—Amines
    • A61K8/415—Aminophenols
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00—Preparations for care of the hair
    • A61Q5/10—Preparations for permanently dyeing the hair

Definitions

  • the present invention relates to agents for the oxidative dyeing of keratin fibers, in particular human hair, containing 4-amino-biphenyl-3-ol derivatives.
  • Oxidation dyes have become very important in the field of coloring keratin fibers, in particular hair coloring.
  • the coloration arises from the reaction of certain developer substances with certain coupler substances in the presence of a suitable oxidizing agent.
  • 2,5-diaminotoluene, 2,5-diaminophenylethyl alcohol, p-aminophenol, 1,4-diaminobenzene and 4,5-diamino-1- (2-hydroxyethyl) pyrazole are used as developer substances, while resorcinol, 2 -Methyl-resorcinol, 1-naphthol, 3-aminophenol, m-phenylene-diamine, 2-amino-4- (2'-hydroxyethyl) amino-anisole, 1, 3-diamino-4- (2'-hydroxyethoxy) benzene and 2,4-diamino-5-fluorotoluene are mentioned.
  • oxidation dyes which are used to dye human hair.
  • the dyes have to be harmless from a toxicological and dermatological point of view, and the hair colorations achieved should have good light fastness, perm, fastness to rubbing and stability to shampooing and sufficient resistance to Have perspiration. It is also necessary that a wide range of different color shades can be produced by combining suitable developer substances and coupler substances.
  • DE-OS 28 33 989 proposes the use of 6-amino-3-methylphenol as an oxidative yellow dye in oxidative hair dyes to solve the problem described.
  • This compound is said to have good suitability as a shading dye for producing light blonde tones and gold tones, although the requirements made, in particular with regard to the resistance of the hair colors to the action of permanent waving agents, are not fully met.
  • the present invention therefore relates to an agent for the oxidative dyeing of keratin fibers, which is characterized in that it contains at least one 4-aminobiphenyl-3-ol derivative of the general formula (I) or its physiologically tolerable, water-soluble salts,
  • R1 and R2 independently of one another are hydrogen, a halogen atom, a cyano group, a hydroxy group, a C 1 -C 4 alkoxy group, a C 2 -C 4 hydroxyalkoxy group, a C, -C 6 alkyl group, a nitro group, a trifluoromethane group , one -C (0) H group, a -C (O) CH 3 group, a -C (0) CF 3 group, a -Si (CH 3 ) 3 group or a C, -C 6 hydroxyalkyl - mean group, or R1 and R2 together form an -O-CH2-O- bridge.
  • Preferred compounds of the formula (I) are those in which (i) R1 is hydrogen and / or (ii) R2 is hydrogen, a methyl group, a trifluoromethyl group, a fluorine atom or a chlorine atom.
  • the following compounds of the formula (I) are particularly preferred: 4-amino-biphenyl-3-ol, 4-amino-2'-chlorobiphenyl-3-ol, 4-amino-3'-chlorobiphenyl-3- ol, 4-amino-4'-chlorobiphenyl-3-ol, 4-amino-2'-fluoro-biphenyl-3-ol, 4-amino-3 , -fluorobiphenyl-3-ol, 4-amino -4'-fluoro-biphenyl-3-ol and their physiologically tolerable salts.
  • the 4-aminobiphenyl-3-ol derivatives of the formula (I) according to the invention can be prepared using known synthetic processes; for example by a palladium (O) catalyzed coupling of a substituted benzene of the formula (II)
  • Rb represents a halogen atom and Rd represents B (OH) 2
  • Rb represents B (OH) 2 and Rd represents a halogen atom
  • R1 and R2 has the meaning given in the formula (I); with subsequent reduction and splitting off of the protective group.
  • the compounds of formula (I) according to the invention enable dyeings with excellent color fastness, in particular with regard to wash fastness and rub fastness as well as permanent wave fastness.
  • the 4-aminobiphenyl-3-ol derivative of the formula (I) is present in the colorant according to the invention in an amount of about 0.001 to 5 percent by weight, an amount of about 0.005 to 2 percent by weight and in particular 0.01 to 1 percent by weight is preferred.
  • the compounds of formula (I) dye keratin fibers, especially human hair, without the addition of further dyes in yellow
  • one or more conventional pxidative dyes for example developer substances or Coupler substances, alone or in a mixture with one another, are added.
  • Coupling substances used here are, in particular, N- (3-dimethylamino-phenyl) urea, 2,6-diamino-pyridine, 2-amino-4 - [(2-hydroxyethyl) amino] anisole, 2,4- Diamino-1-fluoro-5-methyl-benzene, 2,4-diamino-1-methoxy-5-methyl-benzene, 2,4-diamino-1-ethoxy-5-methyl-benzene, 2,4-diamino 1- (2-hydroxyethoxy) -5-methyl-benzene, 2,4-di [(2-hydroxyethyl) amino] -1, 5-dimethoxy-benzene, 2,3-diamino-6-methoxy-pyridine, 3-amino-6-methoxy-2- (methylamino) pyridine, 2,6-diamino-3,5-dimethoxy-pyridine, 3,5-diamino-2,6-dimethoxy-pyridine
  • 1,4-Diamino-benzene (p-phenylenediamine), 1,4-diamino-2-methyl-benzene (p-toluenediamine), 1,4-diamino-2,6-dimethyl-benzene, 1,4 4-diamino-3,5-diethyl-benzene, 1,4-diamino-2,5-dimethyl-benzene, 1,4-diamino-2,3-dimethyl-benzene, 2-chloro-1,4-diaminobenzene, 1,4-diamino-2- (thiophene-2-yl) benzene, 1,4-diamino-2- (thiophene-3-yl) benzene, 4- (2,5-diaminophenyl) -2 - ((diethyl- amino) methyl) thiophene, 2-chloro-3- (2,5-diaminophenyl) thiophene,
  • the total amount of the aforementioned developer substances and coupler substances in the agent according to the invention is about 0.01 to 12 percent by weight, in particular about 0.2 to 6 percent by weight.
  • the colorant according to the invention can also contain other color components, for example 4- (2,5-diamino-benzylamino) aniline or 3- (2,5-diamino-benzylamino) aniline, and also conventional natural, nature-identical or synthetic direct dyes from the Group of anionic (acidic) and cationic (basic) dyes, triarylmethane dyes, nitro dyes, disperse dyes and azo dyes, for example natural dyes such as indigo or henna, triphenylmethane dyes such as 4 - [(4'-amino-phenyl) - ( 4'imino-2 ", 5" -cyclohexadien-1 "-ylidene) -methyl] -2-methyl-aminobenzene-monohydrochloride (Cl 42 510) and 4 - [(4 , -amino-3'-methyl-phenyl) - (4 "-imino-3" -methyl)
  • the aforementioned developer substances and / or coupler substances and / or other color components in combination with the compounds of the formula (I) according to the invention enable a large number of different color shades. For example, by using a combination of the compounds of formula (I) with 4- (2,5-diamino-benzylamino) aniline, it is possible to achieve blonde to brown hair colorations.
  • the coupler substances and developer substances as well as the other color components can also be in the form of their physiologically compatible salts with organic or inorganic acids, such as hydrochloric acid or sulfuric acid, or - if they have aromatic OH groups - in the form of the salts
  • organic or inorganic acids such as hydrochloric acid or sulfuric acid
  • Bases for example as alkali phenolates, can be used.
  • the colorants may also contain other customary cosmetic additives, for example antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite, and also perfume oils, complexing agents, wetting agents, emulsifiers, thickeners and care agents.
  • antioxidants such as ascorbic acid, thioglycolic acid or sodium sulfite
  • perfume oils such as ascorbic acid, thioglycolic acid or sodium sulfite
  • complexing agents such ascorbic acid, thioglycolic acid or sodium sulfite
  • wetting agents such ascorbic acid, thioglycolic acid or sodium sulfite
  • perfume oils such ascorbic acid, thioglycolic acid or sodium sulfite
  • complexing agents such ascorbic acid, thioglycolic acid or sodium sulfite
  • wetting agents such ascorbic acid, thioglycolic acid or sodium sulfite
  • the preparation form of the colorant according to the invention can, for example, be a solution, in particular an aqueous or aqueous-alcoholic solution, a paste, a cream, a gel, an emulsion or be an aerosol preparation.
  • Their composition represents a mixture of the dye components with the additives customary for such preparations.
  • Usual additives in solutions, creams, emulsions or gels are, for example, solvents such as water, lower aliphatic alcohols, for example ethanol, propanol or isopropanol, glycerol or glycols such as 1,2-propylene glycol, furthermore wetting agents or emulsifiers from the classes of the anionic, cationic, amphoteric or nonionic surfactants such as fatty alcohol sulfates, ethoxylated fatty alcohol sulfates, alkylsulfonates, alkylbenzenesulfonates, alkyltrimethylammonium salts, alkylbetaines, oxyethylated fatty alcohols, oxyethylated nonylphenols, fatty acid alkanolamides and oxyethylated fatty acid ester, also thickeners such as higher fatty alcohols, starch, cellulose derivatives, petrolatum, paraffin oil and fatty acids, and
  • ingredients mentioned are used in the amounts customary for such purposes, for example the wetting agents and emulsifiers in concentrations of about 0.5 to 30 percent by weight, the thickeners in an amount of about 0.1 to 30 percent by weight and the care substances in a concentration of about 0.1 to 5 weight percent.
  • the colorant according to the invention can react weakly acidic, neutral or alkaline.
  • it has a pH of 6.5 to 11.5
  • the basic adjustment preferably using ammonia or organic amines, for example monoethanolamine and triethanolamine, or else amino acids or inorganic bases such as sodium hydroxide and potassium hydroxide.
  • ammonia or organic amines for example monoethanolamine and triethanolamine
  • amino acids or inorganic bases such as sodium hydroxide and potassium hydroxide.
  • Inorganic or organic acids for example phosphoric acid, acetic acid, citric acid or tartaric acid, are suitable for pH adjustment in the acidic range.
  • the colorant described above is mixed with an oxidizing agent immediately before use, and an amount sufficient for the hair dyeing treatment, depending on the fullness of the hair, generally about 60 to 200 grams, of this mixture is applied to the hair.
  • the main oxidizing agents used to develop hair color are hydrogen peroxide or its addition compounds with urea, melamine, sodium borate or sodium carbonate in the form of a 3 to 12 percent, preferably ⁇ percent, aqueous solution, but also atmospheric oxygen. If a ⁇ percent hydrogen peroxide solution is used as the oxidizing agent, the weight ratio between hair dye and oxidizing agent is 5: 1 to 1: 2, but preferably 1: 1. Larger amounts of oxidizing agent are used above all at higher dye concentrations in the hair dye or when more bleaching of the hair is intended at the same time.
  • the mixture is allowed to act on the hair at 15 to 50 degrees Celsius for about 10 to 45 minutes, preferably 30 minutes, then the hair is rinsed with water and dried. If necessary, this rinse is washed with a shampoo and, if necessary, with a weak organic acid, such as Example citric acid or tartaric acid, rinsed. The hair is then dried.
  • the hair colorants according to the invention with a content of 4-aminobiphenyl-3-ol derivatives of the formula (I) enable hair colorations with excellent color fastness, in particular with regard to light fastness, wash fastness and rub fastness as well as permanent wave fastness.
  • the hair colorants according to the invention offer a wide range of different color shades, depending on the type and composition of the color components, which ranges from blonde to brown, purple, violet to blue and black shades. The shades are characterized by their special color intensity and a good color balance between damaged and undamaged hair.
  • the very good coloring properties of the hair colorants according to the present application are further shown in the fact that these agents enable graying, chemically not previously damaged hair to be colored easily and with good coverage.
  • the present invention further provides 4-aminobiphenyl-3-ol derivatives of the formula (I), the 4-aminobiphenyl-3-ol and 4-amino-2'-chlorobiphenyl-3- ol, the 4-amino-3'-chlorobiphenyl-3-ol, the 4-amino-4'-chlorobiphenyl-3-ol, the 4-amino-2'-fluorobiphenyl-3-ol, 4-amino-3'-fluoro-biphenyl-3-ol and 4-amino-4'-fluoro-biphenyl-3-ol and their physiologically tolerable salts are particularly preferred.
  • reaction mixture is poured into 100 ml of ethyl acetate, the organic phase is extracted with dilute sodium hydroxide solution and then dried with magnesium sulfate.
  • the Solvent is distilled off on a rotary evaporator and the
  • the product thus obtained is heated to 50 ° C. in 50 ml of ethanol.
  • reaction mixture is poured into 100 ml of ethyl acetate, the organic phase is extracted with dilute sodium hydroxide solution and then dried with magnesium sulfate. The solvent is distilled off on a rotary evaporator and the residue is purified on silica gel with hexane / ethyl acetate (9: 1).
  • the product thus obtained is heated to 50 ° C. in 50 ml of ethanol. 80 ml of a 2.9 molar ethanolic hydrochloric acid solution are then added dropwise. The reaction mixture is cooled to 0 ° C. The precipitate is filtered off, washed twice with 20 ml of ethanol and then dried.
  • Cream-shaped ink carrier compositions of the following composition are produced:

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
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  • Epidemiology (AREA)
  • Cosmetics (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des composés de formule (I) et des agents contenant ces dérivés de 4-amino-biphényl-3-ol de formule générale (I) permettant de colorer des fibres de kératine, notamment des cheveux. R1 et R2 représentent indépendamment l'un de l'autre hydrogène, un atome d'halogène, un groupe cyano, un groupe hydroxy, un groupe alkoxy C1-C4, un groupe hydroxyalkoxy C2-C4, un groupe alkyle C1-C6, un groupe nitro, un groupe trifluorométhane, un groupe -C(O)H-, un groupe -C(O)CH3-, un groupe -C(O)CF3-, un groupe -Si(CH3)3- ou un groupe hydroxyalkyle C1-C6, ou R1 et R2 forment conjointement un pont -O-CH2-O-.
PCT/EP2003/004960 2002-11-02 2003-05-13 Agents contenant des derives de 4-amino-biphenyl-3-ol permettant de colorer des fibres de keratine WO2004041226A1 (fr)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2004548708A JP2006511496A (ja) 2002-11-02 2003-05-13 ４‐アミノ‐ビフェニル‐３‐オール誘導体を含有したケラチン繊維の染色用薬剤
AU2003227748A AU2003227748A1 (en) 2002-11-02 2003-05-13 Agents for dyeing keratin fibers, containing 4-amino-biphenyl-3-ol-derivatives
US10/501,833 US7122061B2 (en) 2002-11-02 2003-05-13 Agents for dyeing keratin fibers, containing 4-aminobiphenyl-3-ol-derivatives
BR0306686-0A BR0306686A (pt) 2002-11-02 2003-05-13 Agentes contendo derivados de 4-amino-bifenil-3-ol para tingir fibras de queratina
EP03725188A EP1562539A1 (fr) 2002-11-02 2003-05-13 Agents contenant des derives de 4-amino-biphenyl-3-ol permettant de colorer des fibres de keratine

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10251106.3 2002-11-02
DE10251106A DE10251106A1 (de) 2002-11-02 2002-11-02 4-Amino-biphenyl-3-ol-Derivate enthaltende Mittel zum Färben von Keratinfasern

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WO2004041226A1 true WO2004041226A1 (fr) 2004-05-21

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PCT/EP2003/004960 WO2004041226A1 (fr) 2002-11-02 2003-05-13 Agents contenant des derives de 4-amino-biphenyl-3-ol permettant de colorer des fibres de keratine

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US (1) US7122061B2 (fr)
EP (1) EP1562539A1 (fr)
JP (1) JP2006511496A (fr)
AU (1) AU2003227748A1 (fr)
BR (1) BR0306686A (fr)
DE (1) DE10251106A1 (fr)
WO (1) WO2004041226A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006007896A1 (fr) * 2004-07-20 2006-01-26 Wella Aktiengesellschaft Nouveaux derives de o-aminophenol, et colorants contenant ces composes

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102004002604A1 (de) * 2004-01-15 2005-08-04 Beiersdorf Ag Visualisierung von Sonnenschutzmitteln auf der Haut

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3577411A (en) * 1964-09-01 1971-05-04 Ciba Ltd 6-phenylbenzazolyl derivatives
US6262113B1 (en) * 1996-03-20 2001-07-17 Smithkline Beecham Corporation IL-8 receptor antagonists
US6380235B1 (en) * 1999-05-04 2002-04-30 American Home Products Corporation Benzimidazolones and analogues
DE10141722A1 (de) * 2001-08-25 2003-03-06 Wella Ag 3-Aminophenol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 3-Aminophenol-Derivate

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2833989A1 (de) * 1978-08-03 1980-02-21 Wella Ag Mittel zum faerben von haaren

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3577411A (en) * 1964-09-01 1971-05-04 Ciba Ltd 6-phenylbenzazolyl derivatives
US6262113B1 (en) * 1996-03-20 2001-07-17 Smithkline Beecham Corporation IL-8 receptor antagonists
US6380235B1 (en) * 1999-05-04 2002-04-30 American Home Products Corporation Benzimidazolones and analogues
DE10141722A1 (de) * 2001-08-25 2003-03-06 Wella Ag 3-Aminophenol-Derivate enthaltende Oxidationshaarfärbemittel sowie neue 3-Aminophenol-Derivate

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
BRADSHAW L.: "The Metabolism of the carcinogen 4-aminobiphenyl and related compounds", ACTA UNIO INTERNATIONALIS CONTRA CANCRUM, vol. 15, 1959, pages 137 - 141, XP009016419 *
LAHAM S., FARANT J.P., POTVIN M.: "Identification of bladder carcinogens by paper chromatography", INDUSTRIAL MEDICINE, vol. 39, no. 3, 1970, pages 142 - 147, XP009016418 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2006007896A1 (fr) * 2004-07-20 2006-01-26 Wella Aktiengesellschaft Nouveaux derives de o-aminophenol, et colorants contenant ces composes
US7641702B2 (en) 2004-07-20 2010-01-05 Wella Ag O-Aminophenol derivatives and colorants containing said compounds

Also Published As

Publication number Publication date
AU2003227748A1 (en) 2004-06-07
BR0306686A (pt) 2004-12-07
JP2006511496A (ja) 2006-04-06
US20050155160A1 (en) 2005-07-21
DE10251106A1 (de) 2004-05-19
US7122061B2 (en) 2006-10-17
EP1562539A1 (fr) 2005-08-17

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